{{chembox | Reference = <ref name="extoxnet">[https://pmep.cce.cornell.edu/profiles/extoxnet/24d-captan/acetochlor-ext.html Cornell University Extension Toxicology Network Pesticide Information Profile on Acetochlor]</ref> | ImageFile = 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide 200.svg | PIN = 2-Chloro-''N''-(ethoxymethyl)-''N''-(2-ethyl-6-methylphenyl)acetamide | OtherNames = Azetochlor<br/>CP55097<br/>ICIA-5676 |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 1911 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C10925 | InChI = 1/C14H20ClNO2/c1-4-12-8-6-7-11(3)14(12)16(10-18-5-2)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3 | InChIKey = VTNQPKFIQCLBDU-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C14H20ClNO2/c1-4-12-8-6-7-11(3)14(12)16(10-18-5-2)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VTNQPKFIQCLBDU-UHFFFAOYSA-N | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1517425 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 34256-82-1 | PubChem = 1988 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 8L08WMO94K | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 2394 | SMILES = ClCC(=O)N(c1c(cccc1CC)C)COCC }} |Section2={{Chembox Properties | C=14 | H=20 | Cl=1 | N=1 | O=2 | Appearance = | Density = 1.100 at 30 °C<br>1.136 at 20 °C | MeltingPt = < | MeltingPtC = 0 | BoilingPt = | Solubility = 223 ppm }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = > | FlashPtC = 100 | AutoignitionPt = }} }} '''Acetochlor''' is an herbicide developed by Monsanto Company and Zeneca. It is a member of the class of herbicides known as chloroacetanilides. Its mode of action is elongase inhibition, and inhibition of geranylgeranyl pyrophosphate (GGPP) cyclization enzymes, part of the gibberellin pathway. It carries high risks of environmental contamination.<ref>{{Cite journal | doi = 10.1002/ps.1935 | pmid = 20232283 | year = 2010 | last1 = Arregui | first1 = M. | last2 = Sánchez | first2 = D. | last3 = Althaus | first3 = R. | last4 = Scotta | first4 = R. | last5 = Bertolaccini | first5 = I. | title = Assessing the risk of pesticide environmental impact in several Argentinian cropping systems with a fuzzy expert indicator | journal = Pest Management Science | volume = 66 | issue = 7 | pages = 736–740 }}</ref> ==Manufacture== Acetochlor is manufactured in two steps from 2-ethyl-6-methylaniline. A reaction with chloroacetyl chloride gives an anilide which is treated with chloromethyl ethyl ether and sodium hydroxide to form the herbicide.<ref>{{cite book |isbn=0815514018 |url=https://books.google.com/books?id=-9cHDi8OOO4C&pg=PA7 | title=Pesticide Synthesis Handbook | last1=Unger | first1=Thomas A. | date=31 December 1996 | publisher=William Andrew |page=7 }}</ref> :550px
==Uses== In the United States, acetochlor was registered by the EPA as a direct substitute for many herbicides of known concern. The EPA imposed several restrictions and conditions on the use of acetochlor.<ref name="EPA">{{cite web|url=http://www.regulations.gov/#!documentDetail;D=EPA-HQ-OPP-2007-0725-0002|title=Acetochlor|publisher=EPA|access-date=2 April 2010}}</ref>
It is approved for pre-emergence application or for pre-planting application with soil incorporation, in corn. (maize) at 5 litres / hectare (1835g / hectare of a.i.)<ref>{{cite web|url=http://e-phy.agriculture.gouv.fr/|title=e-phy|work=agriculture.gouv.fr|access-date=17 May 2015|archive-date=1 June 2003|archive-url=https://web.archive.org/web/20030601205604/http://e-phy.agriculture.gouv.fr/|url-status=dead}}</ref> It is the main active ingredient in Acenit, Keystone, Guardian, Harness, Relay, Sacemid, Surpass, Top-Hand, Trophy and Winner.
It is used to control weeds in corn, and is particularly useful as a replacement for atrazine in the case of some important weeds.
=== Internationally === It is also registered in South Africa.<ref>{{cite web |title=Pesticides Registered in South Africa - EnviroScope.org.za |url=https://enviroscope.org.za/pesticides-registered-in-south-africa/ |publisher=Enviroscope |access-date=5 March 2026 |date=16 November 2024}}</ref>
==Safety== Acetochlor has been classified as a probable human carcinogen.<ref name="extoxnet"/><ref name="EPA"/> Acetochlor, as alachlor, can cause nasal turbinate tumors via the generation of a common tissue reactive metabolite that leads to cytotoxicity and regenerative proliferation in the nasal epithelium.<ref>{{cite web|url=http://www.epa.gov/pesticides/cumulative/chloro_cumulative_risk.pdf|archive-url=https://web.archive.org/web/20080520155101/http://epa.gov/pesticides/cumulative/chloro_cumulative_risk.pdf|url-status=dead|archive-date=May 20, 2008|title=Cumulative Risk Assessment for the Chloroacetanilides|date=2006-03-29|publisher=EPA|access-date=2 April 2010}}</ref>
It is a thyroid disruptor.<ref>{{Cite journal | doi = 10.1289/ehp.7992 | pmid = 16263516 | year = 2005 | last1 = Turque | first1 = N. | last2 = Palmier | first2 = K. | last3 = Le Mével | first3 = S. | last4 = Alliot | first4 = C. | last5 = Demeneix | first5 = B. A. | title = A Rapid, Physiologic Protocol for Testing Transcriptional Effects of Thyroid-Disrupting Agents in Premetamorphic Xenopus Tadpoles | volume = 113 | issue = 11 | pages = 1588–1593 | pmc = 1310923 | journal = Environmental Health Perspectives }}</ref>{{npsn|date=October 2016}}
Human health effects from acetochlor at low environmental doses or at biomonitored levels from low environmental exposures are unknown.<ref>{{cite web|url=https://www.cdc.gov/exposurereport/data_tables/Acetochlor_ChemicalInformation.html |title=National Report on Human Exposure to Environmental Chemicals |date=11 February 2010 |publisher=CDC |access-date=2 April 2010 |url-status=dead |archive-url=https://web.archive.org/web/20110605045858/http://www.cdc.gov/exposurereport/data_tables/Acetochlor_ChemicalInformation.html |archive-date=5 June 2011 }}</ref> A case of poisoning with extremely swollen genitals as a symptom was reported after contact.<ref>{{cite journal | url=| doi=10.1016/j.eucr.2018.10.014 | title=Acetochlor poisoning presenting as acute genital edema: A case report | year=2019 | last1=Tian | first1=Runhui | last2=Liu | first2=Lingyun | last3=Liang | first3=Zuowen | last4=Guo | first4=Kaimin | journal=Urology Case Reports | volume=22 | pages=47–48 | pmid=30406020 | pmc=6214889 }}</ref>
=== Ecologic effects === In the United States, acetochlor is the third most frequently detected herbicide in natural waters.<ref>{{Cite journal| doi = 10.1038/ismej.2007.99| pmid = 18180747| year = 2008| last1 = Foley | first1 = M.| last2 = Sigler | first2 = V.| last3 = Gruden | first3 = C.| title = A multiphasic characterization of the impact of the herbicide acetochlor on freshwater bacterial communities.| volume = 2| issue = 1| pages = 56–66| journal = The ISME Journal | doi-access = free}}</ref>
Acetochlor can accelerate metamorphosis in amphibians.<ref name="auto">{{Cite journal | doi = 10.1016/j.aquatox.2009.06.002 | title = Effects of exposure to acetochlor on the expression of thyroid hormone related genes in larval and adult rare minnow (Gobiocypris rarus) | year = 2009 | last1 = Li | first1 = W. | last2 = Zha | first2 = J. | last3 = Li | first3 = Z. | last4 = Yang | first4 = L. | last5 = Wang | first5 = Z. | journal = Aquatic Toxicology | volume = 94 | pages = 87–93 | pmid = 19577311 | issue = 2 | url = http://ir.rcees.ac.cn/handle/311016/21670 | url-access = subscription | archive-date = 2022-05-13 | access-date = 2019-07-11 | archive-url = https://web.archive.org/web/20220513013310/https://ir.rcees.ac.cn/handle/311016/21670 | url-status = dead }}</ref> It can also affect the development of fish.<ref name="auto"/>
==See also== *Metolachlor
==References== {{reflist|2}}
==External links== * {{PPDB|12}} *[https://web.archive.org/web/20060411075158/http://www.epa.gov/oppefed1/aceto/ U.S. Environmental Protection Agency article on Acetochlor]
{{Herbicides}} {{Aniline Herbicides}}
Category:Herbicides Category:Organochlorides Category:Ethers Category:Endocrine disruptors Category:Acetanilides Category:Group 15 herbicides Category:Anilide herbicides